Visible-light-promoted oxidative halogenation of alkynes

In nature, halogenation promotes the biological activity of secondary metabolites, especially geminal dihalogenation. Related natural molecules have been studied for decades. In recent years, their diversified vital activities have been explored for treating various diseases, which call for efficien...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-11, Vol.55 (95), p.14299-1432
Main Authors: Li, Yiming, Mou, Tao, Lu, Lingling, Jiang, Xuefeng
Format: Article
Language:English
Subjects:
Alkynes
Biological activity
Catalysts
Crystallography
Electron transfer
Halogenation
Metabolites
Room temperature
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Summary:In nature, halogenation promotes the biological activity of secondary metabolites, especially geminal dihalogenation. Related natural molecules have been studied for decades. In recent years, their diversified vital activities have been explored for treating various diseases, which call for efficient and divergent synthetic strategies to facilitate drug discovery. Here we report a catalyst-free oxidative halogenation achieved under ambient conditions (halide ion, air, water, visible light, room temperature, and normal pressure). Constitutionally, electron transfer between the oxygen and halide ion is shuttled via simple conjugated molecules, in which phenylacetylene works as both reactant and catalyst. Synthetically, it provides a highly compatible late-stage transformation strategy to build up dihaloacetophenones (DHAPs). In nature, halogenation promotes the biological activity of secondary metabolites, especially geminal dihalogenation.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc07655g